Compare booking a vacation today with how you (or someone you know) did it 15 or 20 years ago, before the internet had really taken off. It appears that nothing is the same. Imagine collecting recommendations from friends without Twitter and Facebook, researching destinations without Google, comparing and booking flights without sites like Kayak or, more recently, Hipmunk. Surely, the vacation booking industry has undergone major innovation… Hasn’t it?

No. While we use different tools today, we are performing the exact same tasks as we did before. After deciding to take a vacation, we start the process with a broad survey of possibilities, often collected through friends and family. Once we have a more manageable number of options, we research the details of each potential location, validating what we have been told and determining which is the best fit for us. Finally, once we are pretty sure where we would like to go, we compare prices across airlines and hotels, and eventually book our trip.

As illustrated below (my first infographic – not sure if I should be excited or embarrassed), it is clear that most of the innovation in this space has been on the margin, in the tools we use. Sure, these tools are now faster, easier-to-use, able to access more data, but is this real innovation? I do not think so. The process remains the same.

Not much has changed in the vacation booking process

While I argue there hasn’t been much innovation in this space on a whole, I do think there is one major exception. As Sarah Lacy argues in a discussion with Paul Carr here, this exception is the hotel flash-sale sites. These sites reverse the flow of ideas and information. The potential vacationer doesn’t need to do any outbound searches for inspiration – ideas are provided to them. No validation of hotels is necessary – all properties are pre-screened to ensure they meet the high standards of the site’s discerning customers. Price comparisons are pointless – at 40-60% off, users already know they are getting the best deal out there. These sites allow for vacations to be booked in a completely different process. This is remarkable innovation.

The process with hotel deal sites is completely different

As is probably clear at this point, I am a big fan of these sites, but I believe they have one major flaw: they are too narrowly focused. A vacation is made up by a lot more than hotels. Even with these sites, users still need to resort to the outbound search process for the other components of their vacations. Our startup, Itinerie, is seeking to address this gap in the market by selling full vacation packages with this same model. Our sales will include nights in 2-4 hotels, internal transportation, tour guides, cooking classes, et cetera. If you’ve booked a vacation with us, your Itinerie is already complete.

Companies can’t seem to get into this market fast enough, which is fair, as all it takes is a slick website and a persistently charming sales rep to start the business. Thousands of “luxury” rooms go unsold everyday, it’s not that hard to sign the hotels up on the promise of helping them unload some of that extra inventory. And once you’ve got your website and your products, the economics are beautiful. Sure there’s some sales and marketing, but for the most part you can just sit back and collect your commission as users and hotels connect on your platform.

Easy, right? No wonder there are already so many players in this market. No, not quite. User acquisition is the hardest, and often most overlooked, step in the process. The most successful companies in this space have leveraged big advantages in that arena. Jetsetter, for example, was built off of Gilt Groupe’s existing userbase (1.5M at Jetsetter’s launch). SniqueAway and Vacationist are younger and as such still unproven, but they are both backed by large, well-respected brands: TripAdvisor and Travel+Leisure, respectively.

So what’s next? I think the proliferation of new entrants to this market is going to continue at least through the first half of 2011, most with some unique twist on the idea or a specific niche to target. In the long run though, this market will consolidate. Users, the critical variable in the equation, can only put up with so many daily, or even weekly, emails. In the hotel deal site space there has been no GroupOn – no company that captured the majority of the market before anyone else jumped in – but I have no doubt it will end with a similar, winner-take-most market fragmentation.

The company that will win this market will be the one that builds the largest and most dedicated userbase. While no doubt smaller companies will emerge along the way with innovative new product offerings and marketing strategies, players with pre-established userbases will quickly copy or acquire them in order to maintain their lead. The nature of the product offerings still has a long way to go in 2011, but I think we’ve already seen the masthead of the future winner.